When reflecting on his childhood on the South Side of Chicago, Law Roach recalls happy weekends with his grandmother, Eloise.
He’d play outside, eat her freshly baked cookies and observe her Saturday-night preparation for church the next morning.
“Her ritual was to figure out what dress she would wear and what shoes she would wear,” said Roach, who now lives in Los Angeles. “All those things: taking a long bath and doing her nails and her toes and putting the rollers in her hair.”
Roach, who got his own new set of church clothes each year, would tag along with her to Greater Pleasant Green Missionary Baptist Church on Sundays.
“I think that stuck with me: that feeling of wanting to be dressed up, and to feel put together and to be proud of that,” he said.
Now an award-winning fashion stylist and self-described “image architect,” Roach, 46, shares such anecdotes in his new book, “How to Build a Fashion Icon,” which will be released Tuesday. As part of a nationwide tour, Roach will return home for a discussion and book-signing presented by Chicago Humanities Sunday at Thalia Hall.
Known for his work with Zendaya, Céline Dion, Anya Taylor-Joy and many other A-list celebrities, Roach also provides a peek at his process, as well as tips for boosting confidence, in the book.
“I’m so blessed to say when it comes to being a stylist, I have realized all my dreams,” he said. “So, I’m beginning to dream new dreams. But everything moving forward to me is in service to people in a different type of way.”
About 15 years ago, Roach first started to make a name for himself in Pilsen, where he and his friend, Siobhan Strong, ran their own vintage clothing boutique, Deliciously Vintage, on South Halsted Street.
“It just became a place where the cool kids would hang out,” Roach said. “We were surrounded by galleries, and I think it was starting to become this place where creatives would just meet up. It was a beautiful time in my life. It was freedom. It was the first time I felt like I really had something to call my own and to be proud of.”
Roach’s profile rose when Ye (formerly Kanye West) visited the store. Before long, Roach was styling his own clients, including a teenage Zendaya. With his career gaining momentum, he relocated to Los Angeles in 2014.
Roach said he and Zendaya clicked instantly.
“It was something that was so magical,” he recalled. “We just kind of understood each other, right from the very start.”
Roach has since helped Zendaya become a fashion icon. Whether it’s her show-stopping looks at the Met Gala (she was a co-chair at the 2024 event), her Thierry Mugler robot suit at the world premiere of “Dune: Part Two,” or her eclectic ensembles on the media tour for “Challengers,” her outfits continuously make headlines.
“I think it’s our partnership and her confidence,” Roach said of the keys to their success. “She’s able to become whoever this character is that we dream up in our heads when she steps on a carpet.”
Roach said getting the call to work with Céline Dion in 2016 was a major turning point in his career.
“My whole world changed,” he said. “My name recognition changed. That was really the pivotal moment in my life.”
Roach said his favorite look for Dion was her outfit at the 2017 Billboard Awards: a white, Stephane Rolland gown with “cloudlike” sleeves.
“It was just so emotional,” Roach said of working with Dion, who performed “My Heart Will Go On” in honor of the 20th anniversary of “Titanic.”
“The dress was perfect, the voice was perfect. The ambiance, the staging, everything was just so perfect. I think that was the first time that I’ve ever shed a tear at my work. Sometimes I even go back and watch that performance because it was just so perfectly beautiful.”
Following her diagnosis with stiff person syndrome, Dion took a break from working. When she made a public appearance at this year’s Grammy Awards, she called Roach to style her for the occasion.
“I was just like the rest of the world, silently saying a prayer for her every single night,” said Roach, who also styled her for the cover of Vogue France this year. “I just had so much gratitude that she chose me to be a part of that moment with her.”
Beyond styling, Roach is known for his work on TV shows “OMG Fashun,” “Legendary” and “America’s Next Top Model.” Though he hasn’t lived in Chicago in 10 years, he still misses the food, including Italian Fiesta Pizzeria and barbecue from Coleman’s, and even the cold weather.
“I tell people all the time that Chicago gives you this armor where you suffer through the winter so that you can really enjoy the summer,” he said. “And we all get that sense of euphoria when it’s that first nice day and everybody’s so excited and wants to be outside. I actually kind of miss that.”
As part of his quest to give back, Roach has acquired “School of Style,” an online education platform that provides fashion courses.
“I’m really proud of that because I think we’ll be able to take a lot of the red tape and the bureaucracy out of getting into the industry,” he said.
When asked for advice on looking and feeling good, Roach said confidence is key.
“We’re all born with confidence,” he explained. “I think the world steals that from us. The world tells us that we’re not pretty enough or thin enough or smart enough. Growing up being a very feminine boy with the last name Roach, I was destined to be bullied.”
But he learned to feel empowered by his uniqueness instead of ashamed, he said.
“Once you hear my name, you’ll never forget it,” he added. “It’s so undeniably recognizable. And then my mannerisms and the way I carry myself and the way I speak has also made me unforgettable. … That really helped me build my confidence and make my confidence unshakable.”